Experimental. Crystal data. C 20 H 27 N 2 + C 4 H 3 O 4 M r = Orthorhombic, Pna2 1 a = (4) Å b = (4) Å c = 40.

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1 organic compounds Acta Crystallographica Section E Structure Reports Online ISSN Trimipraminium maleate Jerry P. Jasinski, a * Ray J. Butcher, b Q. N. M. Hakim Al-Arique, c H. S. Yathirajan c and B. Narayana d a Department of Chemistry, Keene State College, 229 Main Street, Keene, NH , USA, b Department of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA, c Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore , India, and d Department of Studies in Chemistry, Mangalore University, Mangalagangotri , India Correspondence jjasinski@keene.edu Experimental Crystal data C 20 H 27 N 2 + C 4 H 3 O 4 M r = Orthorhombic, Pna2 1 a = (4) Å b = (4) Å c = (13) Å V = (5) Å 3 Z =16 Cu K radiation = 0.69 mm 1 T = 110 K mm Received 1 January 2010; accepted 4 January 2010 Key indicators: single-crystal X-ray study; T = 110 K; mean (C C) = Å; R factor = 0.038; wr factor = 0.095; data-to-parameter ratio = The title compound [systematic name: 3-(10,11-dihydro-5Hdibenzo[b,f]azepin-5-yl)-N,N,2-trimethylpropan-1-aminium hydrogen maleate], C 20 H 27 N 2 + C 4 H 3 O 4, a maleate salt of trimipramine, crystallizes with four independent cation anion pairs in the asymmetric unit. The trimipramine cation contains a seven-membered azepine ring with two fused benzene rings whose mean planes are separated by 51.7 (1). Intermolecular N HO and intramolecular O HO hydrogen bonds pack the ions into chains along [101]. Additional weak intermolecular C HO interactions help to influence the twist angles of the mean planes of the benzene rings fused to the azepine ring in the cation. A geometry-optimized MOPAC AM1 theoretical calculation supports these observations. Related literature For refractory depression treatment, see: Broquet, (1999). For tricyclic antidepressant treatment, see: Biederman et al. (1989). For treatment of depression, see: Al-Badr, (1983); Al- Badr & Ibrahim (1979); Lapierre, (1989). For protonation of trimipramine salts of maleate, mesylate and hydrochloride observed by 1 H, 13 C and 15 N NMR, see: Somashekar et al. (2004). For the PMR spectrometric analysis of trimipramine maleate in pharmaceutical preparations, see: Al-Badr & Ibrahim (1979). For related structures, see: Bindya et al. (2007); Harrison, Bindya et al. (2007); Harrison, Swamy et al. (2007); Jones et al. (1978); Kamel et al. (2001); Portalone et al. (2007); Post et al. (1975); Swamy et al. (2007). For MOPAC AM1 calculations, see: Schmidt & Polik (2007). For bondlength data, see: Allen et al. (1987). Data collection Oxford Diffraction Xcalibur diffractometer with a Ruby (Gemini Cu) detector Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007) T min = 0.576, T max = Refinement R[F 2 >2(F 2 )] = wr(f 2 ) = S = reflections 1099 parameters 1 restraint Table 1 Hydrogen-bond geometry (Å, ) measured reflections (8810) independent reflections (7507) reflections with I >2(I) R int = H-atom parameters constrained max = 0.25 e Å 3 min = 0.20 e Å 3 Absolute structure: Flack (1983), 8810 Friedel pairs Flack parameter: 0.14 (13) D HA D H HA DA D HA O3A H3AO1A (2) 161 O3B H3BO1B (2) 167 O3C H3CO1C (3) 177 O3D H3DO1D (3) 178 N2E H2EBO2A (3) 156 N2F H2FBO2B (3) 156 N2G H2GBO2C (3) 158 N2H H2HBO4D (3) 158 N2H H2HBO3D (3) 131 C17E H17CO2A (4) 159 C18E H18BO2D i (3) 174 C18F H18CO4C ii (3) 174 C18G H18EO2B (3) 171 C18G H18FO3C iii (3) 154 C18G H18FO4C iii (3) 152 C18H H18GO2A (3) 173 C18H H18HO1D iv (3) 155 C18H H18HO2D iv (3) 152 C19E H19AO4D (3) 118 C19F H19EO4B iv (3) 158 C19G H19IO4B v (3) 163 C19H H19KO4A ii (3) 164 C20E H20AO4A vi (3) 159 C20G H20HO4C iii (3) 149 C20H H20KO2D iv (3) 148 Symmetry codes: (i) x þ 1 2 ; y þ 3 2 ; z; (ii) x 1 2 ; y þ 1 2 ; z; (iii) x 1 2 ; y 1 2 ; z; (iv) x þ 1 2 ; y þ 1 2 ; z; (v) x þ 1 2 ; y 1 2 ; z; (vi) x 1 2 ; y þ 3 2 ; z. o366 Jasinski et al. doi: /s

2 organic compounds Data collection: CrysAlis PRO (Oxford Diffraction, 2007); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL. QNMHA thanks the University of Mysore for use of their research facilities. RJB acknowledges the NSF MRI program (grant No. CHE ) for funds to purchase an X-ray diffractometer. Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NG2715). References Al-Badr, A. A. (1983). Anal. Prof. Drug Subs. 12, Al-Badr, A. A. & Ibrahim, S. E. (1979). Spectrosc. Lett. 12, Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1 19. Biederman, J., Baldessarini, R., Wright, V., Knee, D. & Harmatz, J. (1989). J. Am. Acad. Child Adolesc. Psychiatry, 28, Bindya, S., Wong, W.-T., Ashok, M. A., Yathirajan, H. S. & Rathore, R. S. (2007). Acta Cryst. C63, o546 o548. Broquet, K. (1999). South Med. J. 92, Flack, H. D. (1983). Acta Cryst. A39, Harrison, W. T. A., Bindya, S., Ashok, M. A., Yathirajan, H. S. & Narayana, B. (2007). Acta Cryst. E63, o3143. Harrison, W. T. A., Swamy, M. T., Nagaraja, P., Yathirajan, H. S. & Narayana, B. (2007). Acta Cryst. E63, o3892. Jones, P. G., Kennard, O. & Horn, A. S. (1978). Acta Cryst. B34, Kamel, L. T., El Essawi, M., Wartchow, R. & Berthold, H. J. (2001). Z. Kristallogr. New Cryst. Struct. 216, Lapierre, Y. D. (1989). Drugs, 38, Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED). Oxford Diffraction Ltd, Abingdon, England. Portalone, G., Colapietro, M., Bindya, S., Ashok, M. A. & Yathirajan, H. S. (2007). Acta Cryst. E63, o746 o747. Post, M. L., Kennard, O. & Horn, A. S. (1975). Acta Cryst. B31, Schmidt, J. R. & Polik, W. F. (2007). WebMO Pro. WebMO, LLC, Holland, MI, USA, available from Sheldrick, G. M. (2008). Acta Cryst. A64, Somashekar, B. S., Nagana Gowda, G. A., Ramesha, A. R. & Khetrapal, C. L. (2004). Magn. Res. Chem. 43, Swamy, M. T., Ashok, M. A., Yathirajan, H. S., Narayana, B. & Bolte, M. (2007). Acta Cryst. E63, o4919. Jasinski et al. C 20 H 27 N 2 + C 4 H 3 O 4 o367

3 supporting information [ Trimipraminium maleate Jerry P. Jasinski, Ray J. Butcher, Q. N. M. Hakim Al-Arique, H. S. Yathirajan and B. Narayana S1. Comment The title compound is a derivative of trimipramine, chemically, 5-(3-dimethylamino-2-methylpropyl)-10,11-dihydro-5Hdibenz(b,f)azepine maleate, a tricyclic antidepressant with sedative and anxiolytic properties and available as stangyl, surmontil, rhotrimine and generic forms. Tricyclic antidepressants are sometimes still used to treat refractory depression that has failed to respond to standard SSRI therapy (Broquet, 1999). Tricyclic antidepressants have been shown to be effective in treating attention-deficit hyperactivity disorder(adhd) (Biederman et al., 1989). ADHD is thought to be caused by dopamine and norepinephrine shortages in the brain's prefrontal cortex. Trimipramine is a tricyclic antidepressant of the dibenzazepine class with sedative properties. It also has anticholinergic properties and potentiates the sympathetic response, presumably by blocking the reuptake of norepinephrine which has been released by the presynaptic neurons. It has a quinidine like effect on the heart and an EEG activity similar to that of other tricyclic antidepressants. Trimipramine is a serotonin transport blocker that also blocks norepinephrine uptake. The mechanism of action of trimipramine differs from other tricyclic antidepressants. It is only a moderate reuptake inhibitor of norepinephrine, and a weak reuptake inhibitor of serotonin and dopamine. The spectrum of effects (strong antidepressant activity, sedation and anxiolysis) and side-effects (strong anticholinergic and antiadrenergic side-effects) is the same as with Doxepin. It is also a more effective sedative than amitriptyline. Trimipramine is the only effective drug against insomnia known so far that does not alter the normal sleep architecture. Trimipramine maleate salt is used in the treatment of depression as well as peptic ulcer and severe chronic pain. A comprehensive description of the title compound is described (Al-Badr, 1983; Lapierre, 1989). The protonation of trimipramine salts of maleate, mesylate and hydrochloride observed by 1 H, 13 C and 15 N NMR spectroscopy is reported (Somashekar et al., 2004). Also, the PMR spectrometric analysis of trimipramine maleate in pharmaceutical preparation is described (Al-Badr & Ibrahim, 1979). The related crystal structures viz., imipramine hydrochloride (Post et al., 1975), 5-(3-dimethylammonioprop-1-enylidene)-5H-dibenzo[a,d]cycloheptene maleate (Jones et al., 1978), desipraminium picrate (Swamy et al., 2007), desipraminium picrate monohydrate (Harrison, Swamy et al., 2007), imipraminium picrate (Harrison, Bindya et al., 2007), amitriptylinium picrate (Bindya et al., 2007), 5-[3-(dimethylamino)propyl]-10,11-dihydro-5H-dibenz[a,d][7]annulen-5-ol (Portalone et al., 2007) have been reported. In view of the importance of the title compound, a crystal structure is reported. The title compound, C 20 H 27 N 2+. C 4 H 3 O 4-, a maleate salt of trimipramine, crystallizes with four independent cation-anion pairs (E A, Fig.1; F B, Fig. 2; G C, Fig. 3; H D, Fig. 4) in the asymmetric unit. Bond lengths and bond angles are all within expected ranges (Allen et al. 1987). The Trimipramine cation, C 20 H 27 N 2+, contains a seven-membered azepine ring with two fused benzene rings whose mean planes are separated by 51.3 (8) [E], 51.7 (6) [F], 49.9 (0) [G], and 53.9 (0) [H], respectively. These angles are all less than 57;1(1) reported for bis((3-(10,11-dihydrodibenzo(b,f)azepin-5-yl)-2-methyl-propyl) dimethylammonium) tetrachlorocuprate(ii) (Kamel et al. 2001), which contains an identical cation. Intermolecular N H O and intramolecular O H O hydrogen bonds (Table 1, Fig. 5) sup-1

4 pack the ions into chains along the [101]. Additional weak C H O intermolecular interactions (Table 1) help to significantly influence the twist angles of the mean planes of the benzene rings fused to the azepine ring in the cation. After a geometry optimimized MOPAC AM1 calculation with WebMO Pro (Schmidt & Polik 2007) on the cation fragment, in vacuo, the dihedral angle between the mean planes of the two benzene rings of the azepine group becomes 51.3 (8), which is slightly less than the average of the four indepentent cations (51.7 (1) but nearly 6 less than that observed in the tetrachlorocuprate (ii) analogue compound. These observations support the suggestion that these intra and intermolecular interactions influence crystal packing in the title compound. S2. Experimental The title compound was obtained as a gift sample from R. L. Fine Chem, Bangalore, India. The compound was used without further purification. X-ray quality crystals (m.p K) were obtained by slow evaporation from methanol solution. S3. Refinement All of the H atoms were placed in their calculated positions and then refined using the riding model with O H = 0.84 Å, N H = 0.93 Å, C H = Å, and with U iso (H) = U eq (O), U iso (H) = eq (N), U iso (H) = U eq (C). Figure 1 ORTEP drawings of cation E (C 20 H 27 N 2+ ) and anion A (C 4 H 3 O 4- ) in the asymmetric unit of (I) showing the atom numbering scheme and 50% probability displacement ellipsoids of non-h atoms. Dashed lines indicate N2E H2EB O2A intermolecular and O3A H3A O1A intramolecular hydrogen bond interactions. sup-2

5 Figure 2 ORTEP drawings of cation F (C 20 H 27 N 2+ ) and anion B (C 4 H 3 O 4- ) in the asymmetric unit of (I) showing the atom numbering scheme and 50% probability displacement ellipsoids of non-h atoms. Dashed lines indicate N2F H2FB O2B intermolecular and O3B H3B O1B intramolecular hydrogen bond interactions. Figure 3 ORTEP drawings of cation G (C 20 H 27 N 2+ ) and anion C (C 4 H 3 O 4- ) in the asymmetric unit of (I) showing the atom numbering scheme and 50% probability displacement ellipsoids of non-h atoms. Dashed lines indicate N2G H2GB O2C intermolecular and O3C H3C O1C intramolecular hydrogen bond interactions. sup-3

6 Figure 4 ORTEP drawings of cation H (C 20 H 27 N 2+ ) and anion D (C 4 H 3 O 4- ) in the asymmetric unit of (I) showing the atom numbering scheme and 50% probability displacement ellipsoids of non-h atoms. Dashed lines indicate N2H H2HB O4C and N2H H2HB O3D intermolecular and O3D H3D O1D intramolecular hydrogen bond interactions. Figure The molecular packing for (I) viewed down the b axis. Dashed lines indicate cation C 20 H 27 N 2 and anion C 4 H 3 O 4 inter and intramolecular hydrogen bond interactions linking the ions into chains along the [101]. sup-4

7 3-(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)- N,N,2-trimethylpropan-1-aminium hydrogen maleate Crystal data C 20 H 27 N 2+ C 4 H 3 O 4 M r = Orthorhombic, Pna2 1 Hall symbol: P 2c -2n a = (4) Å b = (4) Å c = (13) Å V = (5) Å 3 Z = 16 Data collection Oxford Diffraction Xcalibur diffractometer with a Ruby (Gemini Cu) detector Radiation source: Enhance (Cu) X-ray Source Graphite monochromator Detector resolution: pixels mm -1 ω scans Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007) Refinement Refinement on F 2 Least-squares matrix: full R[F 2 > 2σ(F 2 )] = wr(f 2 ) = S = reflections 1099 parameters 1 restraint Primary atom site location: structure-invariant direct methods Secondary atom site location: difference Fourier map F(000) = 3520 D x = Mg m 3 Cu Kα radiation, λ = Å Cell parameters from reflections θ = µ = 0.69 mm 1 T = 110 K Plate, colorless mm T min = 0.576, T max = measured reflections (8810) independent reflections (7507) reflections with I > 2σ(I) R int = θ max = 74.3, θ min = 4.2 h = k = l = Hydrogen site location: inferred from neighbouring sites H-atom parameters constrained w = 1/[σ 2 (F o2 ) + (0.0612P) 2 ] where P = (F o 2 + 2F c2 )/3 (Δ/σ) max = Δρ max = 0.25 e Å 3 Δρ min = 0.20 e Å 3 Absolute structure: Flack (1983), 8810 Friedel pairs Absolute structure parameter: 0.14 (13) Special details Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. Refinement. Refinement of F 2 against ALL reflections. The weighted R-factor wr and goodness of fit S are based on F 2, conventional R-factors R are based on F, with F set to zero for negative F 2. The threshold expression of F 2 > σ(f 2 ) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å 2 ) x y z U iso */U eq O1A (9) (15) (5) (4) O2A (8) (16) (5) (4) O3A (9) (16) (5) (4) sup-5

8 H3A * O4A (8) (18) (4) (4) C1A (11) (2) (6) (5) C2A (12) (2) (6) (5) H2AA * C3A (12) (2) (6) (5) H3AA * C4A (12) (2) (6) (5) O1B (9) (15) (5) (4) O2B (8) (16) (5) (4) O3B (9) (16) (5) (4) H3B * O4B (8) (18) (4) (4) C1B (11) (2) (6) (5) C2B (12) (2) (6) (5) H2BA * C3B (12) (2) (6) (5) H3BA * C4B (12) (2) (6) (5) O1C (9) (17) (6) (5) O2C (8) (15) (5) (4) O3C (9) (18) (6) (5) H3C (10)* O4C (9) (17) (5) (5) C1C (12) (2) (6) (5) C2C (12) (2) (6) (5) H2CA * C3C (12) (2) (6) (5) H3CA * C4C (12) (2) (7) (5) O1D (9) (18) (6) (5) O2D (9) (17) (6) (5) O3D (9) (18) (6) (5) H3D (15)* O4D (8) (16) (5) (4) C1D (12) (2) (7) (6) C2D (12) (2) (7) (5) H2DA * C3D (12) (2) (6) (5) H3DA * C4D (12) (2) (6) (5) N1E (10) (19) (5) (4) N2E (12) (17) (6) (5) H2EB * C1E (14) (2) (7) (6) C2E (13) (2) (7) (5) H2EA * C3E (15) (3) (8) (7) sup-6

9 H3EA * C4E (15) (3) (9) (8) H4EA * C5E (14) (3) (8) (7) H5EA * C6E (15) (3) (8) (7) C7E (14) (3) (7) (8) H7EA * H7EB * C8E (15) (3) (7) (8) H8EA * H8EB * C9E (13) (3) (6) (6) C10E (14) (3) (8) (7) H10A * C11E (15) (3) (10) (8) H11A * C12E (15) (3) (9) (7) H12A * C13E (13) (3) (7) (6) H13A * C14E (12) (2) (6) (5) C15E (12) (2) (6) (5) H15A * H15B * C16E (15) (2) (7) (6) H16A * C17E (13) (3) (8) (6) H17A * H17B * H17C * C18E (12) (2) (6) (5) H18A * H18B * C19E (13) (2) (7) (6) H19A * H19B * H19C * C20E (13) (2) (6) (5) H20A * H20B * H20C * N1F (9) (18) (5) (4) N2F (11) (17) (6) (5) H2FB * C1F (11) (2) (6) (5) C2F (13) (2) (6) (5) H2FA * sup-7

10 C3F (14) (3) (7) (6) H3FA * C4F (14) (3) (8) (7) H4FA * C5F (13) (2) (7) (6) H5FA * C6F (12) (2) (6) (5) C7F (14) (3) (7) (6) H7FA * H7FB * C8F (13) (3) (6) (6) H8FA * H8FB * C9F (14) (3) (7) (6) C10F (13) (3) (7) (6) H10B * C11F (14) (2) (8) (7) H11B * C12F (14) (3) (8) (6) H12B * C13F (13) (2) (6) (5) H13B * C14F (15) (2) (7) (6) C15F (11) (2) (6) (5) H15C * H15D * C16F (14) (2) (7) (6) H16B * C17F (12) (3) (7) (6) H17D * H17E * H17F * C18F (11) (2) (6) (5) H18C * H18D * C19F (13) (2) (6) (5) H19D * H19E * H19F * C20F (12) (2) (7) (6) H20D * H20E * H20F * N1G (11) (2) (5) (4) N2G (11) (19) (6) (5) H2GB * C1G (13) (2) (6) (5) C2G (12) (2) (6) (5) sup-8

11 H2GA * C3G (13) (3) (6) (6) H3GA * C4G (14) (3) (7) (6) H4GA * C5G (14) (3) (7) (6) H5GA * C6G (12) (2) (6) (5) C7G (12) (2) (6) (5) H7GA * H7GB * C8G (14) (2) (6) (6) H8GA * H8GB * C9G (15) (2) (8) (6) C10G (14) (3) (7) (6) H10C * C11G (14) (2) (7) (6) H11C * C12G (14) (3) (7) (6) H12C * C13G (13) (2) (7) (5) H13C * C14G (14) (2) (8) (6) C15G (12) (2) (6) (5) H15E * H15F * C16G (11) (2) (6) (4) H16C * C17G (12) (2) (6) (5) H17G * H17H * H17I * C18G (11) (2) (6) (5) H18E * H18F * C19G (13) (2) (7) (6) H19G * H19H * H19I * C20G (14) (3) (6) (7) H20G * H20H * H20I * N1H (10) (19) (5) (4) N2H (11) (18) (5) (4) H2HB * C1H (12) (2) (6) (5) sup-9

12 C2H (11) (2) (6) (5) H2HA * C3H (13) (2) (6) (5) H3HA * C4H (14) (2) (6) (5) H4HA * C5H (13) (2) (6) (5) H5HA * C6H (12) (2) (6) (5) C7H (13) (2) (7) (6) H7HA * H7HB * C8H (14) (2) (7) (6) H8HA * H8HB * C9H (15) (2) (8) (6) C10H (15) (3) (7) (6) H10D * C11H (15) (3) (7) (6) H11D * C12H (14) (3) (8) (6) H12D * C13H (13) (2) (7) (6) H13D * C14H (14) (2) (7) (6) C15H (12) (2) (6) (5) H15G * H15H * C16H (11) (2) (5) (4) H16D * C17H (13) (2) (6) (5) H17J * H17K * H17L * C18H (11) (2) (6) (5) H18G * H18H * C19H (13) (2) (7) (5) H19J * H19K * H19L * C20H (14) (3) (6) (7) H20J * H20K * H20L * sup-10

13 Atomic displacement parameters (Å 2 ) U 11 U 22 U 33 U 12 U 13 U 23 O1A (8) (9) (11) (7) (8) (8) O2A (8) (10) (11) (7) (8) (9) O3A (8) (10) (10) (7) (8) (8) O4A (8) (12) (10) (8) (7) (8) C1A (11) (12) (12) (9) (9) (10) C2A (11) (11) (12) (9) (9) (10) C3A (11) (12) (11) (9) (9) (10) C4A (11) (14) (11) (10) (9) (10) O1B (8) (9) (11) (7) (8) (8) O2B (8) (10) (10) (7) (8) (8) O3B (8) (9) (10) (7) (8) (8) O4B (8) (11) (9) (8) (7) (8) C1B (10) (12) (11) (9) (9) (10) C2B (11) (12) (12) (9) (10) (10) C3B (11) (12) (12) (9) (10) (10) C4B (11) (13) (11) (9) (9) (10) O1C (9) (10) (14) (7) (9) (10) O2C (8) (9) (10) (7) (7) (8) O3C (9) (11) (14) (8) (9) (10) O4C (8) (10) (13) (7) (8) (9) C1C (11) (11) (12) (9) (9) (10) C2C (11) (12) (13) (10) (10) (10) C3C (12) (12) (13) (10) (10) (10) C4C (11) (12) (15) (9) (10) (11) O1D (8) (11) (14) (8) (9) (10) O2D (8) (10) (14) (7) (9) (10) O3D (9) (11) (14) (8) (9) (10) O4D (8) (10) (11) (7) (8) (8) C1D (11) (13) (15) (10) (11) (12) C2D (11) (13) (14) (10) (10) (11) C3D (12) (13) (13) (10) (10) (11) C4D (12) (12) (13) (9) (10) (11) N1E (9) (11) (9) (8) (8) (8) N2E (10) (11) (12) (7) (9) (8) C1E (12) (14) (14) (9) (11) (10) C2E (12) (14) (13) (10) (10) (11) C3E (15) (14) (18) (12) (14) (13) C4E (14) (15) (2) (12) (15) (16) C5E (12) (18) (18) (12) (12) (15) C6E (13) (19) (16) (10) (12) (12) C7E (12) (2) (13) (13) (10) (14) C8E (14) (2) (13) (14) (11) (14) C9E (12) (16) (12) (11) (10) (11) C10E (13) (15) (17) (12) (13) (14) C11E (14) (14) (2) (12) (15) (16) sup-11

14 C12E (13) (16) (2) (12) (14) (14) C13E (12) (15) (14) (10) (10) (12) C14E (11) (13) (12) (10) (9) (10) C15E (11) (13) (11) (9) (9) (10) C16E (13) (14) (15) (9) (11) (10) C17E (13) (14) (16) (11) (11) (13) C18E (10) (11) (12) (9) (10) (10) C19E (12) (14) (15) (11) (11) (12) C20E (12) (14) (12) (10) (10) (11) N1F (8) (11) (9) (8) (7) (8) N2F (10) (11) (12) (7) (9) (8) C1F (10) (12) (11) (9) (9) (9) C2F (11) (14) (12) (10) (10) (11) C3F (13) (14) (15) (11) (12) (12) C4F (14) (14) (19) (12) (13) (14) C5F (11) (14) (15) (10) (11) (12) C6F (10) (14) (11) (10) (9) (11) C7F (12) (18) (13) (12) (10) (12) C8F (12) (18) (12) (12) (10) (12) C9F (13) (15) (15) (10) (11) (11) C10F (11) (15) (16) (11) (11) (13) C11F (13) (13) (2) (10) (13) (13) C12F (13) (14) (17) (11) (12) (13) C13F (11) (13) (13) (10) (10) (11) C14F (12) (14) (13) (9) (10) (9) C15F (10) (12) (11) (9) (9) (10) C16F (12) (13) (15) (8) (11) (9) C17F (12) (14) (15) (11) (10) (13) C18F (10) (11) (12) (8) (9) (10) C19F (12) (14) (12) (10) (10) (11) C20F (11) (14) (14) (10) (11) (11) N1G (10) (11) (10) (8) (8) (8) N2G (10) (10) (11) (8) (9) (9) C1G (12) (13) (11) (10) (10) (10) C2G (11) (13) (11) (10) (9) (10) C3G (11) (15) (13) (11) (10) (11) C4G (14) (15) (14) (12) (12) (12) C5G (13) (15) (13) (11) (11) (11) C6G (11) (13) (11) (10) (9) (10) C7G (11) (13) (12) (10) (10) (10) C8G (13) (14) (12) (11) (11) (11) C9G (13) (14) (14) (10) (12) (10) C10G (13) (15) (13) (11) (11) (12) C11G (13) (14) (15) (11) (12) (12) C12G (13) (14) (15) (10) (12) (12) C13G (11) (13) (13) (10) (10) (11) C14G (14) (15) (15) (9) (11) (10) C15G (11) (12) (11) (9) (9) (9) sup-12

15 C16G (10) (11) (11) (9) (9) (9) C17G (11) (12) (12) (9) (10) (10) C18G (10) (12) (11) (10) (9) (10) C19G (13) (12) (14) (10) (11) (11) C20G (14) (19) (12) (13) (11) (13) N1H (10) (11) (10) (8) (8) (8) N2H (10) (10) (11) (8) (8) (8) C1H (12) (13) (11) (9) (9) (10) C2H (10) (13) (10) (9) (9) (9) C3H (11) (13) (11) (10) (9) (10) C4H (13) (11) (12) (10) (11) (10) C5H (13) (13) (12) (10) (10) (10) C6H (11) (13) (12) (10) (9) (10) C7H (12) (14) (13) (10) (10) (11) C8H (13) (14) (13) (11) (11) (11) C9H (13) (15) (14) (10) (11) (10) C10H (14) (15) (13) (12) (12) (11) C11H (16) (14) (15) (12) (12) (12) C12H (14) (14) (16) (11) (12) (12) C13H (12) (13) (12) (10) (10) (11) C14H (13) (13) (14) (9) (11) (9) C15H (10) (12) (11) (9) (9) (10) C16H (10) (11) (11) (8) (9) (9) C17H (12) (13) (13) (10) (10) (11) C18H (10) (12) (12) (9) (9) (11) C19H (12) (11) (14) (10) (11) (11) C20H (13) (2) (12) (13) (11) (13) Geometric parameters (Å, º) O1A C1A (3) C12F H12B O2A C1A (3) C13F C14F (4) O3A C4A (3) C13F H13B O3A H3A C15F C16F (4) O4A C4A (3) C15F H15C C1A C2A (3) C15F H15D C2A C3A (3) C16F C18F (4) C2A H2AA C16F C17F (3) C3A C4A (3) C16F H16B C3A H3AA C17F H17D O1B C1B (3) C17F H17E O2B C1B (3) C17F H17F O3B C4B (3) C18F H18C O3B H3B C18F H18D O4B C4B (3) C19F H19D C1B C2B (3) C19F H19E C2B C3B (3) C19F H19F C2B H2BA C20F H20D sup-13

16 C3B C4B (3) C20F H20E C3B H3BA C20F H20F O1C C1C (3) N1G C14G (3) O2C C1C (3) N1G C1G (3) O3C C4C (3) N1G C15G (3) O3C H3C N2G C20G (3) O4C C4C (3) N2G C19G (3) C1C C2C (3) N2G C18G (3) C2C C3C (3) N2G H2GB C2C H2CA C1G C6G (4) C3C C4C (4) C1G C2G (4) C3C H3CA C2G C3G (4) O1D C1D (3) C2G H2GA O2D C1D (3) C3G C4G (4) O3D C4D (3) C3G H3GA O3D H3D C4G C5G (4) O4D C4D (3) C4G H4GA C1D C2D (4) C5G C6G (4) C2D C3D (3) C5G H5GA C2D H2DA C6G C7G (3) C3D C4D (3) C7G C8G (4) C3D H3DA C7G H7GA N1E C14E (3) C7G H7GB N1E C1E (3) C8G C9G (4) N1E C15E (3) C8G H8GA N2E C20E (3) C8G H8GB N2E C19E (3) C9G C10G (4) N2E C18E (3) C9G C14G (4) N2E H2EB C10G C11G (4) C1E C2E (4) C10G H10C C1E C6E (4) C11G C12G (4) C2E C3E (4) C11G H11C C2E H2EA C12G C13G (4) C3E C4E (5) C12G H12C C3E H3EA C13G C14G (4) C4E C5E (5) C13G H13C C4E H4EA C15G C16G (3) C5E C6E (4) C15G H15E C5E H5EA C15G H15F C6E C7E (5) C16G C18G (3) C7E C8E (5) C16G C17G (3) C7E H7EA C16G H16C C7E H7EB C17G H17G C8E C9E (4) C17G H17H C8E H8EA C17G H17I C8E H8EB C18G H18E C9E C10E (4) C18G H18F C9E C14E (4) C19G H19G sup-14

17 C10E C11E (5) C19G H19H C10E H10A C19G H19I C11E C12E (5) C20G H20G C11E H11A C20G H20H C12E C13E (4) C20G H20I C12E H12A N1H C1H (3) C13E C14E (4) N1H C14H (3) C13E H13A N1H C15H (3) C15E C16E (4) N2H C20H (3) C15E H15A N2H C19H (3) C15E H15B N2H C18H (3) C16E C18E (4) N2H H2HB C16E C17E (4) C1H C2H (3) C16E H16A C1H C6H (4) C17E H17A C2H C3H (4) C17E H17B C2H H2HA C17E H17C C3H C4H (4) C18E H18A C3H H3HA C18E H18B C4H C5H (4) C19E H19A C4H H4HA C19E H19B C5H C6H (4) C19E H19C C5H H5HA C20E H20A C6H C7H (3) C20E H20B C7H C8H (4) C20E H20C C7H H7HA N1F C14F (3) C7H H7HB N1F C1F (3) C8H C9H (4) N1F C15F (3) C8H H8HA N2F C20F (3) C8H H8HB N2F C19F (3) C9H C10H (4) N2F C18F (3) C9H C14H (4) N2F H2FB C10H C11H (4) C1F C2F (4) C10H H10D C1F C6F (3) C11H C12H (4) C2F C3F (4) C11H H11D C2F H2FA C12H C13H (4) C3F C4F (4) C12H H12D C3F H3FA C13H C14H (4) C4F C5F (4) C13H H13D C4F H4FA C15H C16H (3) C5F C6F (4) C15H H15G C5F H5FA C15H H15H C6F C7F (4) C16H C18H (3) C7F C8F (4) C16H C17H (3) C7F H7FA C16H H16D C7F H7FB C17H H17J C8F C9F (4) C17H H17K C8F H8FA C17H H17L sup-15

18 C8F H8FB C18H H18G C9F C14F (4) C18H H18H C9F C10F (4) C19H H19J C10F C11F (4) C19H H19K C10F H10B C19H H19L C11F C12F (4) C20H H20J C11F H11B C20H H20K C12F C13F (4) C20H H20L C4A O3A H3A C17F C16F H16B O2A C1A O1A (2) C15F C16F H16B O2A C1A C2A (2) C16F C17F H17D O1A C1A C2A (2) C16F C17F H17E C3A C2A C1A (2) H17D C17F H17E C3A C2A H2AA C16F C17F H17F C1A C2A H2AA H17D C17F H17F C2A C3A C4A (2) H17E C17F H17F C2A C3A H3AA C16F C18F N2F (19) C4A C3A H3AA C16F C18F H18C O4A C4A O3A (2) N2F C18F H18C O4A C4A C3A (2) C16F C18F H18D O3A C4A C3A (2) N2F C18F H18D C4B O3B H3B H18C C18F H18D O2B C1B O1B (2) N2F C19F H19D O2B C1B C2B (2) N2F C19F H19E O1B C1B C2B (2) H19D C19F H19E C3B C2B C1B (2) N2F C19F H19F C3B C2B H2BA H19D C19F H19F C1B C2B H2BA H19E C19F H19F C2B C3B C4B (2) N2F C20F H20D C2B C3B H3BA N2F C20F H20E C4B C3B H3BA H20D C20F H20E O4B C4B O3B (2) N2F C20F H20F O4B C4B C3B (2) H20D C20F H20F O3B C4B C3B (2) H20E C20F H20F C4C O3C H3C C14G N1G C1G (2) O2C C1C O1C (2) C14G N1G C15G (2) O2C C1C C2C (2) C1G N1G C15G (2) O1C C1C C2C (2) C20G N2G C19G (2) C3C C2C C1C (2) C20G N2G C18G (2) C3C C2C H2CA C19G N2G C18G (2) C1C C2C H2CA C20G N2G H2GB C2C C3C C4C (2) C19G N2G H2GB C2C C3C H3CA C18G N2G H2GB C4C C3C H3CA C6G C1G C2G (2) O4C C4C O3C (2) C6G C1G N1G (2) O4C C4C C3C (2) C2G C1G N1G (2) O3C C4C C3C (2) C3G C2G C1G (2) sup-16

19 C4D O3D H3D C3G C2G H2GA O2D C1D O1D (3) C1G C2G H2GA O2D C1D C2D (2) C2G C3G C4G (2) O1D C1D C2D (2) C2G C3G H3GA C3D C2D C1D (2) C4G C3G H3GA C3D C2D H2DA C5G C4G C3G (3) C1D C2D H2DA C5G C4G H4GA C2D C3D C4D (2) C3G C4G H4GA C2D C3D H3DA C4G C5G C6G (2) C4D C3D H3DA C4G C5G H5GA O4D C4D O3D (2) C6G C5G H5GA O4D C4D C3D (2) C1G C6G C5G (2) O3D C4D C3D (2) C1G C6G C7G (2) C14E N1E C1E (2) C5G C6G C7G (2) C14E N1E C15E (2) C6G C7G C8G (2) C1E N1E C15E (2) C6G C7G H7GA C20E N2E C19E (2) C8G C7G H7GA C20E N2E C18E (18) C6G C7G H7GB C19E N2E C18E (2) C8G C7G H7GB C20E N2E H2EB H7GA C7G H7GB C19E N2E H2EB C9G C8G C7G (2) C18E N2E H2EB C9G C8G H8GA C2E C1E C6E (3) C7G C8G H8GA C2E C1E N1E (2) C9G C8G H8GB C6E C1E N1E (3) C7G C8G H8GB C1E C2E C3E (3) H8GA C8G H8GB C1E C2E H2EA C10G C9G C14G (3) C3E C2E H2EA C10G C9G C8G (3) C4E C3E C2E (3) C14G C9G C8G (2) C4E C3E H3EA C11G C10G C9G (3) C2E C3E H3EA C11G C10G H10C C3E C4E C5E (3) C9G C10G H10C C3E C4E H4EA C12G C11G C10G (3) C5E C4E H4EA C12G C11G H11C C4E C5E C6E (3) C10G C11G H11C C4E C5E H5EA C11G C12G C13G (3) C6E C5E H5EA C11G C12G H12C C5E C6E C1E (3) C13G C12G H12C C5E C6E C7E (3) C12G C13G C14G (3) C1E C6E C7E (3) C12G C13G H13C C6E C7E C8E (2) C14G C13G H13C C6E C7E H7EA C13G C14G C9G (2) C8E C7E H7EA C13G C14G N1G (3) C6E C7E H7EB C9G C14G N1G (2) C8E C7E H7EB N1G C15G C16G (19) H7EA C7E H7EB N1G C15G H15E C7E C8E C9E (2) C16G C15G H15E C7E C8E H8EA N1G C15G H15F sup-17

20 C9E C8E H8EA C16G C15G H15F C7E C8E H8EB H15E C15G H15F C9E C8E H8EB C18G C16G C17G (2) H8EA C8E H8EB C18G C16G C15G (18) C10E C9E C14E (3) C17G C16G C15G (19) C10E C9E C8E (3) C18G C16G H16C C14E C9E C8E (3) C17G C16G H16C C11E C10E C9E (3) C15G C16G H16C C11E C10E H10A C16G C17G H17G C9E C10E H10A C16G C17G H17H C12E C11E C10E (3) H17G C17G H17H C12E C11E H11A C16G C17G H17I C10E C11E H11A H17G C17G H17I C11E C12E C13E (3) H17H C17G H17I C11E C12E H12A N2G C18G C16G (19) C13E C12E H12A N2G C18G H18E C12E C13E C14E (3) C16G C18G H18E C12E C13E H13A N2G C18G H18F C14E C13E H13A C16G C18G H18F C13E C14E C9E (3) H18E C18G H18F C13E C14E N1E (2) N2G C19G H19G C9E C14E N1E (2) N2G C19G H19H N1E C15E C16E (2) H19G C19G H19H N1E C15E H15A N2G C19G H19I C16E C15E H15A H19G C19G H19I N1E C15E H15B H19H C19G H19I C16E C15E H15B N2G C20G H20G H15A C15E H15B N2G C20G H20H C15E C16E C18E (2) H20G C20G H20H C15E C16E C17E (2) N2G C20G H20I C18E C16E C17E (2) H20G C20G H20I C15E C16E H16A H20H C20G H20I C18E C16E H16A C1H N1H C14H (2) C17E C16E H16A C1H N1H C15H (2) C16E C17E H17A C14H N1H C15H (2) C16E C17E H17B C20H N2H C19H (2) H17A C17E H17B C20H N2H C18H (2) C16E C17E H17C C19H N2H C18H (2) H17A C17E H17C C20H N2H H2HB H17B C17E H17C C19H N2H H2HB N2E C18E C16E (19) C18H N2H H2HB N2E C18E H18A C2H C1H C6H (2) C16E C18E H18A C2H C1H N1H (2) N2E C18E H18B C6H C1H N1H (2) C16E C18E H18B C3H C2H C1H (2) H18A C18E H18B C3H C2H H2HA N2E C19E H19A C1H C2H H2HA N2E C19E H19B C2H C3H C4H (2) sup-18

21 H19A C19E H19B C2H C3H H3HA N2E C19E H19C C4H C3H H3HA H19A C19E H19C C5H C4H C3H (2) H19B C19E H19C C5H C4H H4HA N2E C20E H20A C3H C4H H4HA N2E C20E H20B C4H C5H C6H (2) H20A C20E H20B C4H C5H H5HA N2E C20E H20C C6H C5H H5HA H20A C20E H20C C5H C6H C1H (2) H20B C20E H20C C5H C6H C7H (2) C14F N1F C1F (19) C1H C6H C7H (2) C14F N1F C15F (2) C6H C7H C8H (2) C1F N1F C15F (19) C6H C7H H7HA C20F N2F C19F (2) C8H C7H H7HA C20F N2F C18F (2) C6H C7H H7HB C19F N2F C18F (18) C8H C7H H7HB C20F N2F H2FB H7HA C7H H7HB C19F N2F H2FB C7H C8H C9H (2) C18F N2F H2FB C7H C8H H8HA C2F C1F C6F (2) C9H C8H H8HA C2F C1F N1F (2) C7H C8H H8HB C6F C1F N1F (2) C9H C8H H8HB C3F C2F C1F (2) H8HA C8H H8HB C3F C2F H2FA C10H C9H C14H (3) C1F C2F H2FA C10H C9H C8H (3) C4F C3F C2F (3) C14H C9H C8H (2) C4F C3F H3FA C11H C10H C9H (3) C2F C3F H3FA C11H C10H H10D C5F C4F C3F (3) C9H C10H H10D C5F C4F H4FA C12H C11H C10H (3) C3F C4F H4FA C12H C11H H11D C4F C5F C6F (3) C10H C11H H11D C4F C5F H5FA C11H C12H C13H (3) C6F C5F H5FA C11H C12H H12D C5F C6F C1F (2) C13H C12H H12D C5F C6F C7F (2) C12H C13H C14H (3) C1F C6F C7F (2) C12H C13H H13D C8F C7F C6F (2) C14H C13H H13D C8F C7F H7FA C13H C14H C9H (2) C6F C7F H7FA C13H C14H N1H (3) C8F C7F H7FB C9H C14H N1H (2) C6F C7F H7FB N1H C15H C16H (18) H7FA C7F H7FB N1H C15H H15G C9F C8F C7F (2) C16H C15H H15G C9F C8F H8FA N1H C15H H15H C7F C8F H8FA C16H C15H H15H C9F C8F H8FB H15G C15H H15H C7F C8F H8FB C18H C16H C17H (2) sup-19

22 H8FA C8F H8FB C18H C16H C15H (18) C14F C9F C10F (3) C17H C16H C15H (19) C14F C9F C8F (2) C18H C16H H16D C10F C9F C8F (3) C17H C16H H16D C11F C10F C9F (3) C15H C16H H16D C11F C10F H10B C16H C17H H17J C9F C10F H10B C16H C17H H17K C12F C11F C10F (3) H17J C17H H17K C12F C11F H11B C16H C17H H17L C10F C11F H11B H17J C17H H17L C13F C12F C11F (3) H17K C17H H17L C13F C12F H12B N2H C18H C16H (18) C11F C12F H12B N2H C18H H18G C12F C13F C14F (3) C16H C18H H18G C12F C13F H13B N2H C18H H18H C14F C13F H13B C16H C18H H18H C13F C14F C9F (3) H18G C18H H18H C13F C14F N1F (2) N2H C19H H19J C9F C14F N1F (2) N2H C19H H19K N1F C15F C16F (2) H19J C19H H19K N1F C15F H15C N2H C19H H19L C16F C15F H15C H19J C19H H19L N1F C15F H15D H19K C19H H19L C16F C15F H15D N2H C20H H20J H15C C15F H15D N2H C20H H20K C18F C16F C17F (2) H20J C20H H20K C18F C16F C15F (19) N2H C20H H20L C17F C16F C15F (2) H20J C20H H20L C18F C16F H16B H20K C20H H20L O2A C1A C2A C3A (3) C1F N1F C14F C9F 71.6 (3) O1A C1A C2A C3A 16.6 (4) C15F N1F C14F C9F (2) C1A C2A C3A C4A 0.3 (4) C14F N1F C15F C16F 67.3 (3) C2A C3A C4A O4A (3) C1F N1F C15F C16F (2) C2A C3A C4A O3A 18.1 (4) N1F C15F C16F C18F 71.8 (3) O2B C1B C2B C3B (3) N1F C15F C16F C17F (2) O1B C1B C2B C3B 17.1 (4) C17F C16F C18F N2F 73.5 (3) C1B C2B C3B C4B 0.8 (5) C15F C16F C18F N2F (19) C2B C3B C4B O4B (3) C20F N2F C18F C16F 76.0 (3) C2B C3B C4B O3B 16.5 (4) C19F N2F C18F C16F (2) O2C C1C C2C C3C (3) C14G N1G C1G C6G 72.0 (3) O1C C1C C2C C3C 5.0 (4) C15G N1G C1G C6G (2) C1C C2C C3C C4C 1.0 (5) C14G N1G C1G C2G (3) C2C C3C C4C O4C (3) C15G N1G C1G C2G 45.0 (3) C2C C3C C4C O3C 2.6 (4) C6G C1G C2G C3G 2.5 (4) O2D C1D C2D C3D (3) N1G C1G C2G C3G (2) O1D C1D C2D C3D 2.7 (4) C1G C2G C3G C4G 2.7 (4) C1D C2D C3D C4D 2.0 (5) C2G C3G C4G C5G 1.4 (4) sup-20

23 C2D C3D C4D O4D (3) C3G C4G C5G C6G 0.1 (4) C2D C3D C4D O3D 6.8 (4) C2G C1G C6G C5G 1.0 (4) C14E N1E C1E C2E (3) N1G C1G C6G C5G (2) C15E N1E C1E C2E 40.9 (3) C2G C1G C6G C7G (2) C14E N1E C1E C6E 72.4 (3) N1G C1G C6G C7G 5.6 (3) C15E N1E C1E C6E (2) C4G C5G C6G C1G 0.2 (4) C6E C1E C2E C3E 0.7 (4) C4G C5G C6G C7G (3) N1E C1E C2E C3E (2) C1G C6G C7G C8G 67.8 (3) C1E C2E C3E C4E 1.3 (4) C5G C6G C7G C8G (3) C2E C3E C4E C5E 1.0 (4) C6G C7G C8G C9G 65.4 (3) C3E C4E C5E C6E 0.0 (4) C7G C8G C9G C10G (3) C4E C5E C6E C1E 0.6 (4) C7G C8G C9G C14G 10.3 (4) C4E C5E C6E C7E (3) C14G C9G C10G C11G 0.4 (4) C2E C1E C6E C5E 0.3 (4) C8G C9G C10G C11G (3) N1E C1E C6E C5E (2) C9G C10G C11G C12G 1.0 (4) C2E C1E C6E C7E (2) C10G C11G C12G C13G 0.5 (4) N1E C1E C6E C7E 1.7 (4) C11G C12G C13G C14G 0.5 (4) C5E C6E C7E C8E (3) C12G C13G C14G C9G 1.1 (4) C1E C6E C7E C8E 70.3 (3) C12G C13G C14G N1G (2) C6E C7E C8E C9E 57.2 (4) C10G C9G C14G C13G 0.7 (4) C7E C8E C9E C10E (2) C8G C9G C14G C13G (3) C7E C8E C9E C14E 5.0 (4) C10G C9G C14G N1G (2) C14E C9E C10E C11E 0.8 (4) C8G C9G C14G N1G 2.5 (4) C8E C9E C10E C11E (3) C1G N1G C14G C13G (3) C9E C10E C11E C12E 1.0 (4) C15G N1G C14G C13G 22.6 (4) C10E C11E C12E C13E 0.9 (5) C1G N1G C14G C9G 48.7 (4) C11E C12E C13E C14E 1.0 (4) C15G N1G C14G C9G (2) C12E C13E C14E C9E 2.8 (4) C14G N1G C15G C16G 70.4 (3) C12E C13E C14E N1E (2) C1G N1G C15G C16G (2) C10E C9E C14E C13E 2.6 (3) N1G C15G C16G C18G (2) C8E C9E C14E C13E (2) N1G C15G C16G C17G 73.5 (3) C10E C9E C14E N1E (2) C20G N2G C18G C16G (2) C8E C9E C14E N1E 4.6 (4) C19G N2G C18G C16G 50.1 (3) C1E N1E C14E C13E (3) C17G C16G C18G N2G 60.5 (3) C15E N1E C14E C13E 26.5 (3) C15G C16G C18G N2G (2) C1E N1E C14E C9E 60.9 (3) C14H N1H C1H C2H (3) C15E N1E C14E C9E (2) C15H N1H C1H C2H 43.2 (3) C14E N1E C15E C16E (2) C14H N1H C1H C6H 73.4 (3) C1E N1E C15E C16E 64.9 (3) C15H N1H C1H C6H (2) N1E C15E C16E C18E 69.9 (3) C6H C1H C2H C3H 3.4 (3) N1E C15E C16E C17E (2) N1H C1H C2H C3H (2) C20E N2E C18E C16E (2) C1H C2H C3H C4H 2.0 (3) C19E N2E C18E C16E 76.4 (3) C2H C3H C4H C5H 0.8 (3) C15E C16E C18E N2E (2) C3H C4H C5H C6H 2.2 (4) C17E C16E C18E N2E 73.2 (3) C4H C5H C6H C1H 0.7 (4) C14F N1F C1F C2F (2) C4H C5H C6H C7H (2) C15F N1F C1F C2F 24.8 (3) C2H C1H C6H C5H 2.1 (4) C14F N1F C1F C6F 59.2 (3) N1H C1H C6H C5H (2) sup-21